Ethanol → 2-Amino-5-(1-ethoxypropyl)pyridine

HRID 600631Notes

Reaction equation

HRID 600631 reaction equation
CC1[N:3]([C:8]2[N:13]=[CH:12][C:11]([CH:14]([OH:17])[CH2:15][CH3:16])=[CH:10][CH:9]=2)C(C)=CC=1.Cl.NO.[CH2:21](O)[CH3:22]>O>[NH2:3][C:8]1[CH:9]=[CH:10][C:11]([CH:14]([O:17][CH2:21][CH3:22])[CH2:15][CH3:16])=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 672732841-[6-(2,5-Dimethylpyrrol-1-yl)pyridin-3-yl]propan-1-ol

Product 1

HCID 672733132-Amino-5-(1-ethoxypropyl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1.07 g of 1-[6-(2,5-dimethylpyrrol-1-yl)pyridin-3-yl]propan-1-ol in 20 mL of ethanol heated to 80° C. is added a solution of 1.94 g of hydroxylamine hydrochloride in 1.6 mL of water, and the mixture is stirred for 24 hours at 80° C. After cooling to room temperature, the reaction medium is filtered and concentrated to dryness. The residue is purified by flash chromatography on a column of 100 g of silica, eluting with 400 mL of dichloromethane, then with 300 mL of ethyl acetate and then with a 95/5 mixture of dichloromethane and methanol. The fractions containing the expected product are combined and concentrated under vacuum to give 0.186 g of 2-amino-5-(1-ethoxypropyl)pyridine in the form of a brown oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction medium is filtered
  3. concentrationconcentrated to dryness
  4. customThe residue is purified by flash chromatography on a column of 100 g of silica
  5. washeluting with 400 mL of dichloromethane
  6. additionwith 300 mL of ethyl acetate and then with a 95/5 mixture of dichloromethane and methanol
  7. additionThe fractions containing the expected product
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ddd69b587e4949b2973267b1d20f912d
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

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